ES2825029T3 - Síntesis de raltegravir - Google Patents

Síntesis de raltegravir Download PDF

Info

Publication number: ES2825029T3
Authority: ES; Spain
Prior art keywords: formula; methyl; compound; oxadiazole; raltegravir
Prior art date: 2011-12-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

ES12862643T

Other languages

English (en)

Spanish (es)

Inventor

Mukund Keshav Gurjar

Swapnil Panditrao Sonawane

Golakchandra Sudarshan Maikap

Gulabrao Dagadu Patil

Shivnath Bhaupatil Shinde

Pankaj Shalikrao Patil

Samit Satish Mehta

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Emcure Pharmaceuticals Ltd

Original Assignee

Emcure Pharmaceuticals Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2011-12-26

Filing date

2012-12-21

Publication date

2021-05-14

2012-12-21 Application filed by Emcure Pharmaceuticals Ltd filed Critical Emcure Pharmaceuticals Ltd

2021-05-14 Application granted granted Critical

2021-05-14 Publication of ES2825029T3 publication Critical patent/ES2825029T3/es

Status Active legal-status Critical Current

2032-12-21 Anticipated expiration legal-status Critical

Links

CZFFBEXEKNGXKS-UHFFFAOYSA-N raltegravir Chemical compound O1C(C)=NN=C1C(=O)NC(C)(C)C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C CZFFBEXEKNGXKS-UHFFFAOYSA-N 0.000 title claims abstract description 41
229960004742 raltegravir Drugs 0.000 title claims abstract description 39
230000015572 biosynthetic process Effects 0.000 title description 19
238000003786 synthesis reaction Methods 0.000 title description 12
238000000034 method Methods 0.000 claims abstract description 36
150000001875 compounds Chemical class 0.000 claims abstract description 28
238000002360 preparation method Methods 0.000 claims abstract description 27
YTPZPNMYRGCCOA-UHFFFAOYSA-N n-(2-cyanopropan-2-yl)-5-methyl-1,3,4-oxadiazole-2-carboxamide Chemical compound CC1=NN=C(C(=O)NC(C)(C)C#N)O1 YTPZPNMYRGCCOA-UHFFFAOYSA-N 0.000 claims abstract description 14
-1 carbonyl oxadiazole chloride Chemical compound 0.000 claims abstract description 11
IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 claims abstract description 8
JQULXIOYDDCNGR-UHFFFAOYSA-N 2-amino-2-methylpropanenitrile Chemical compound CC(C)(N)C#N JQULXIOYDDCNGR-UHFFFAOYSA-N 0.000 claims abstract description 8
239000012022 methylating agents‎ Substances 0.000 claims abstract description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
150000002443 hydroxylamines Chemical class 0.000 claims abstract 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 18
FDSKHNQDEGJGEI-UHFFFAOYSA-N n-[2-[6-[(4-fluorophenyl)methylcarbamoyl]-5-hydroxy-4-oxo-1h-pyrimidin-2-yl]propan-2-yl]-5-methyl-1,3,4-oxadiazole-2-carboxamide Chemical compound O1C(C)=NN=C1C(=O)NC(C)(C)C1=NC(=O)C(O)=C(C(=O)NCC=2C=CC(F)=CC=2)N1 FDSKHNQDEGJGEI-UHFFFAOYSA-N 0.000 claims description 16
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
239000011541 reaction mixture Substances 0.000 claims description 9
YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 claims description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
LBVLPWFXXSJTDR-UHFFFAOYSA-N methyl 5-hydroxy-2-[2-[(5-methyl-1,3,4-oxadiazole-2-carbonyl)amino]propan-2-yl]-4-oxo-1h-pyrimidine-6-carboxylate Chemical compound O=C1C(O)=C(C(=O)OC)NC(C(C)(C)NC(=O)C=2OC(C)=NN=2)=N1 LBVLPWFXXSJTDR-UHFFFAOYSA-N 0.000 claims description 5
BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 claims description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 2
AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical compound C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 claims description 2
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
QDNCLIPKBNMUPP-UHFFFAOYSA-N trimethyloxidanium Chemical compound C[O+](C)C QDNCLIPKBNMUPP-UHFFFAOYSA-N 0.000 claims description 2
238000001816 cooling Methods 0.000 claims 2
230000008878 coupling Effects 0.000 claims 1
238000010168 coupling process Methods 0.000 claims 1
238000005859 coupling reaction Methods 0.000 claims 1
238000010992 reflux Methods 0.000 claims 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract description 2
230000001035 methylating effect Effects 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
239000012535 impurity Substances 0.000 description 12
238000007069 methylation reaction Methods 0.000 description 12
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
230000011987 methylation Effects 0.000 description 8
PSFVIUFHKCHVST-UHFFFAOYSA-N n-[(1z)-1-amino-1-hydroxyimino-2-methylpropan-2-yl]-5-methyl-1,3,4-oxadiazole-2-carboxamide Chemical compound CC1=NN=C(C(=O)NC(C)(C)C(\N)=N\O)O1 PSFVIUFHKCHVST-UHFFFAOYSA-N 0.000 description 7
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
VIFAJZRMLMTNJT-UHFFFAOYSA-N oxadiazole-4-carbonyl chloride Chemical compound ClC(=O)C1=CON=N1 VIFAJZRMLMTNJT-UHFFFAOYSA-N 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000008096 xylene Substances 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 3
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 3
238000010923 batch production Methods 0.000 description 3
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
230000037361 pathway Effects 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
238000000746 purification Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000725303 Human immunodeficiency virus Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000009435 amidation Effects 0.000 description 2
238000007112 amidation reaction Methods 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229940124522 antiretrovirals Drugs 0.000 description 2
239000003903 antiretrovirus agent Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
239000000347 magnesium hydroxide Substances 0.000 description 2
229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
241000694440 Colpidium aqueous Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
101100170601 Drosophila melanogaster Tet gene Proteins 0.000 description 1
208000031886 HIV Infections Diseases 0.000 description 1
241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
102100034343 Integrase Human genes 0.000 description 1
108010061833 Integrases Proteins 0.000 description 1
230000006179 O-acylation Effects 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
241001122767 Theaceae Species 0.000 description 1
RLTPOGIGJILWFY-UHFFFAOYSA-N [N].O=C1N=CC=CN1 Chemical compound [N].O=C1N=CC=CN1 RLTPOGIGJILWFY-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000013020 final formulation Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229940111682 isentress Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
ZZDSUVCMHPGVIG-UHFFFAOYSA-N methyl 5-hydroxy-2-[2-[(5-methyl-1,3,4-oxadiazole-2-carbonyl)amino]propan-2-yl]-6-oxo-1H-pyrimidine-4-carboxylate 1H-pyrimidin-2-one Chemical compound O=c1nccc[nH]1.COC(=O)c1[nH]c(nc(=O)c1O)C(C)(C)NC(=O)c1nnc(C)o1 ZZDSUVCMHPGVIG-UHFFFAOYSA-N 0.000 description 1
OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical group OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

ES12862643T 2011-12-26 2012-12-21 Síntesis de raltegravir Active ES2825029T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IN3664MU2011		2011-12-26
PCT/IN2012/000835 WO2013098854A2 (en)	2011-12-26	2012-12-21	Synthesis of raltegravir

Publications (1)

Publication Number	Publication Date
ES2825029T3 true ES2825029T3 (es)	2021-05-14

Family

ID=48698747

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES12862643T Active ES2825029T3 (es)	2011-12-26	2012-12-21	Síntesis de raltegravir

Country Status (4)

Country	Link
US (2)	US9403809B2 (de)
EP (1)	EP2804607B1 (de)
ES (1)	ES2825029T3 (de)
WO (1)	WO2013098854A2 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP3102565B1 (de) *	2014-02-03	2019-01-02	Mylan Laboratories Ltd.	Verfahren zur herstellung von raltegravir-intermediaten
WO2017220208A1 (en)	2016-06-21	2017-12-28	Pharmathen S.A.	Process for preparing compounds useful as intermediates for the preparation of raltegravir

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL161337A0 (en) *	2001-10-26	2004-09-27	Angeletti P Ist Richerche Bio	N-substituted hydroxypyrimidinone carboxamide inhibitors of hiv integrase
UA87884C2 (uk)	2004-12-03	2009-08-25	Мерк Энд Ко., Инк.	Безводна кристалічна калієва сіль інгібітора віл-інтегрази
WO2007087188A2 (en) *	2006-01-20	2007-08-02	Merck & Co., Inc.	Taste-masked tablets and granules
CN101526489B (zh) *	2008-03-04	2011-10-26	普拉德研究及开发股份有限公司	用于检测油中的石蜡和沥青质的含量的方法

2012
- 2012-12-21 EP EP12862643.9A patent/EP2804607B1/de active Active
- 2012-12-21 ES ES12862643T patent/ES2825029T3/es active Active
- 2012-12-21 US US14/368,460 patent/US9403809B2/en active Active
- 2012-12-21 WO PCT/IN2012/000835 patent/WO2013098854A2/en not_active Ceased
2016
- 2016-06-28 US US15/195,477 patent/US9475799B1/en active Active

Also Published As

Publication number	Publication date
US20150045554A1 (en)	2015-02-12
WO2013098854A2 (en)	2013-07-04
EP2804607B1 (de)	2020-09-16
US9403809B2 (en)	2016-08-02
EP2804607A2 (de)	2014-11-26
WO2013098854A3 (en)	2014-10-02
US20160311810A1 (en)	2016-10-27
US9475799B1 (en)	2016-10-25
EP2804607A4 (de)	2015-08-12

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